AU7261881A - Therapeutically active compounds - Google Patents
Therapeutically active compoundsInfo
- Publication number
- AU7261881A AU7261881A AU72618/81A AU7261881A AU7261881A AU 7261881 A AU7261881 A AU 7261881A AU 72618/81 A AU72618/81 A AU 72618/81A AU 7261881 A AU7261881 A AU 7261881A AU 7261881 A AU7261881 A AU 7261881A
- Authority
- AU
- Australia
- Prior art keywords
- sup
- sub
- group
- groups containing
- active compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/34—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton and at least one hydroxy group bound to another carbon atom of the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Emergency Medicine (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Saccharide Compounds (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Luminescent Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
New bronchospasmolytically active compounds exhibiting long duration of action and reduced undesired side effects of the structural formulaand therapeutically acceptable salts thereof, in which formula R is selected from the group consisting of -C(CH<sub>3</sub>)<sub>3</sub>,andR<sup>1</sup> is selected from the group consisting of H and <sub>R2</sub>, R<sup>2</sup> represents the radical of the formulawherein R<sup>3</sup> is selected from the group consisting of(a) H(b) alkyl groups containing 1-3 carbon atomswherein R<sup>5</sup> is selected from the group consisting of(a) OH(b) alkoxy groups containing 1-3 carbon atoms and whereinR<sup>4</sup> is selected from the group consisting of(a) H(b) alkyl groups containing 1-3 carbon atoms, with the proviso that R<sup>3</sup> and R<sup>4</sup> are combined as follows:processes for the preparation thereof, chemical intermediates at their preparation, pharmaceutical preparations containing them, and their medicinal use.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8022439 | 1980-07-09 | ||
| GB8022439 | 1980-09-07 | ||
| GB8116441 | 1981-05-29 | ||
| GB8116441 | 1981-05-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7261881A true AU7261881A (en) | 1982-01-14 |
| AU539976B2 AU539976B2 (en) | 1984-10-25 |
Family
ID=26276161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU72618/81A Expired AU539976B2 (en) | 1980-07-09 | 1981-07-07 | Therapeutically active compounds |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US4419364A (en) |
| EP (1) | EP0043807B1 (en) |
| KR (3) | KR850000301B1 (en) |
| AT (1) | ATE7689T1 (en) |
| AU (1) | AU539976B2 (en) |
| CA (1) | CA1180021A (en) |
| CS (1) | CS221845B2 (en) |
| CY (1) | CY1273A (en) |
| DD (1) | DD202001A5 (en) |
| DE (1) | DE3163871D1 (en) |
| DK (1) | DK157678C (en) |
| ES (3) | ES503768A0 (en) |
| FI (1) | FI73666C (en) |
| GR (1) | GR74291B (en) |
| HK (1) | HK5385A (en) |
| HU (2) | HU184959B (en) |
| IE (1) | IE51373B1 (en) |
| IS (1) | IS1262B6 (en) |
| LU (1) | LU88304I2 (en) |
| MX (1) | MX9203239A (en) |
| MY (1) | MY8700026A (en) |
| NO (2) | NO152130C (en) |
| NZ (1) | NZ197628A (en) |
| PH (2) | PH16535A (en) |
| PL (1) | PL128513B1 (en) |
| PT (1) | PT73336B (en) |
| SG (1) | SG79784G (en) |
| SU (1) | SU1128830A3 (en) |
| YU (3) | YU42116B (en) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8904064D0 (en) * | 1989-12-01 | 1989-12-01 | Astra Ab | IMPROVED METHOD OF PREPARING AND INTERMEDIATE FOR THE MANUFACTURE OF BAMBUTEROL |
| SE9000948D0 (en) | 1990-03-16 | 1990-03-16 | Draco Ab | NEW USE |
| US5830422A (en) * | 1995-06-23 | 1998-11-03 | Ormiston Mining And Smelting Co. Ltd. | Method for production of sodium bicarbonate, sodium carbonate and ammonium sulfate from sodium sulfate |
| AU2247997A (en) * | 1996-01-29 | 1997-08-20 | Savor, Evelyn P. | Method of treating undesired uterine contractions using optically pure R-or RR-isomers of adrenergic beta-2 agonists |
| SE9604752D0 (en) * | 1996-12-20 | 1996-12-20 | Astra Ab | Formulation and use |
| KR20030085658A (en) * | 2002-04-30 | 2003-11-07 | 한올제약주식회사 | An improved synthetic method of bambuterol |
| JP4979889B2 (en) * | 2002-08-08 | 2012-07-18 | タン,ダブリュー. | Method for producing R-type bambuterol or a pharmaceutically acceptable salt thereof |
| US7495028B2 (en) * | 2002-08-08 | 2009-02-24 | Wen Tan | R-bambuterol, its preparation and therapeutic uses |
| US7825147B2 (en) * | 2003-08-29 | 2010-11-02 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type-IV |
| US20070259874A1 (en) * | 2003-11-26 | 2007-11-08 | Palle Venkata P | Phosphodiesterase Inhibitors |
| WO2006081986A1 (en) * | 2005-02-07 | 2006-08-10 | F.Hoffmann-La Roche Ag | Bambuterol and integrin inhibitor combination |
| US7915286B2 (en) | 2005-09-16 | 2011-03-29 | Ranbaxy Laboratories Limited | Substituted pyrazolo [3,4-b] pyridines as phosphodiesterase inhibitors |
| WO2007045979A1 (en) | 2005-10-19 | 2007-04-26 | Ranbaxy Laboratories Limited | Pharmaceutical compositions of muscarinic receptor antagonists |
| BRPI0617673C1 (en) * | 2005-10-19 | 2012-05-22 | Ranbaxy Lab Ltd | phosphodiesterase type iv inhibitor compositions |
| WO2008023336A2 (en) | 2006-08-22 | 2008-02-28 | Ranbaxy Laboratories Limited | Matrix metalloproteinase inhibitors |
| EP2066661A2 (en) * | 2006-09-22 | 2009-06-10 | Ranbaxy Laboratories Limited | Phosphodiesterase inhibitors |
| WO2008035315A2 (en) * | 2006-09-22 | 2008-03-27 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type-iv |
| EP1958947A1 (en) | 2007-02-15 | 2008-08-20 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type 4 |
| US20110130403A1 (en) * | 2007-03-14 | 2011-06-02 | Ranbaxy Laboratories Limited | Pyrazolo [3, 4-b] pyridine derivatives as phosphodiesterase inhibitors |
| DK2124944T3 (en) | 2007-03-14 | 2012-04-23 | Ranbaxy Lab Ltd | Pyrazolo [3,4-b] pyridine derivatives as phosphodiesterase inhibitors |
| EP2111861A1 (en) | 2008-04-21 | 2009-10-28 | Ranbaxy Laboratories Limited | Compositions of phosphodiesterase type IV inhibitors |
| MX2013001240A (en) | 2010-07-30 | 2013-08-27 | Ranbaxy Lab Ltd | METALOPROTEIN MATRIX INHIBITORS. |
| CN103228634A (en) | 2010-09-24 | 2013-07-31 | 兰贝克赛实验室有限公司 | Matrix metalloproteinase inhibitors |
| WO2014087298A1 (en) | 2012-12-03 | 2014-06-12 | Pfizer Inc. | Novel selective androgen receptor modulators |
| US9784726B2 (en) | 2013-01-08 | 2017-10-10 | Atrogi Ab | Screening method, a kit, a method of treatment and a compound for use in a method of treatment |
| CN104557614B (en) * | 2014-12-15 | 2017-01-04 | 广东东阳光药业有限公司 | A kind of method of reducing of amine |
| CN105622461B (en) * | 2016-01-29 | 2018-06-19 | 华南理工大学 | A kind of compound and its preparation method and application |
| CN105859589B (en) * | 2016-04-05 | 2018-09-28 | 深圳市康立生生物科技有限公司 | A method of preparing bambuterol impurity C |
| GB201714734D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714740D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714736D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714745D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| CN109942462B (en) * | 2019-03-06 | 2022-01-14 | 宏冠生物药业有限公司 | Synthesis process of bambuterol hydrochloride |
| GB201903832D0 (en) | 2019-03-20 | 2019-05-01 | Atrogi Ab | New compounds and methods |
| GB202205895D0 (en) | 2022-04-22 | 2022-06-08 | Atrogi Ab | New medical uses |
| EP4651867A1 (en) | 2023-01-20 | 2025-11-26 | Atrogi AB | Beta 2-adrenergic receptor agonists for treatment or prevention of muscle wasting |
| GB202302225D0 (en) | 2023-02-16 | 2023-04-05 | Atrogi Ab | New medical uses |
| GB202303229D0 (en) | 2023-03-06 | 2023-04-19 | Atrogi Ab | New medical uses |
| CN117586152A (en) * | 2023-11-23 | 2024-02-23 | 黑龙江乌苏里江制药有限公司 | A kind of preparation method of bambuterol hydrochloride |
| GB202403169D0 (en) | 2024-03-05 | 2024-04-17 | Atrogi Ab | New medical uses |
| WO2025238248A1 (en) | 2024-05-17 | 2025-11-20 | Atrogi Ab | USE OF β2-ADRENERGIC RECEPTOR AGONISTS IN TREATING MUSCLE WASTING |
| CN120585720A (en) * | 2025-06-12 | 2025-09-05 | 肇庆学院 | A nasal drug preparation for dual-target drugs and its application |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE178032C1 (en) | 1961-01-01 | |||
| DE1643488U (en) | 1949-11-28 | 1952-09-11 | G E Hilge Fa | INCUBATOR. |
| DK85789C (en) | 1955-07-05 | 1958-06-30 | Cilag Ag | Process for the preparation of d, 1- or 1-isopropyl-aminomethyl- (3,4-dihydroxy-phenyl) -carbinol or salts thereof. |
| DE1768167U (en) | 1958-04-02 | 1958-06-04 | Artur O Herrmann | ROAD OBSTACLE WARNING DEVICE. |
| DE1275069B (en) | 1960-02-15 | 1968-08-14 | Boehringer Sohn Ingelheim | 1- (3 ', 5'-dihydroxyphenyl) -1-hydroxy-2-isopropylaminoalkanes and processes for their preparation |
| NL123439C (en) | 1961-09-14 | |||
| FR1324857A (en) * | 1962-06-14 | 1963-04-19 | Chemie Linz Ag | Process for the preparation of phenylethanolamine derivatives |
| GB1141606A (en) | 1965-04-12 | 1969-01-29 | Rech S Et D Applic Scient Et M | Improvements in alkyl ethers of substituted phenylaminoethanols |
| DE1543372A1 (en) | 1966-10-18 | 1971-04-01 | Boehringer Sohn Ingelheim | Process for the preparation of o-substituted 3,4-dioxyphenylalkanolamines |
| SE358633B (en) | 1966-10-19 | 1973-08-06 | Draco Ab | |
| NO132866C (en) | 1966-10-19 | 1976-01-21 | Draco Ab | |
| US3937838A (en) * | 1966-10-19 | 1976-02-10 | Aktiebolaget Draco | Orally active bronchospasmolytic compounds and their preparation |
| SE335359B (en) | 1966-10-19 | 1971-05-24 | Draco Ab | |
| FR6087M (en) | 1967-01-10 | 1968-06-04 | ||
| SE369299B (en) | 1967-10-18 | 1974-08-19 | Draco Ab | |
| SE338324B (en) | 1967-12-19 | 1971-09-06 | Haessle Ab | |
| GB1298771A (en) | 1969-04-01 | 1972-12-06 | Sterling Drug Inc | Carboxylic esters of hydroxyphenylalkanolamines |
| AT294046B (en) | 1969-07-08 | 1971-11-10 | Chemie Linz Ag | Process for the preparation of N, N'-bis [2- (3 ', 4'-dihydroxyphenyl) -2-hydroxyethyl] -hexamethylenediamine, its optically active forms and the salts thereof |
| US3657319A (en) * | 1970-05-05 | 1972-04-18 | Smith Kline French Lab | Alpha-aminoalkyl-4-hydroxy-3-carboalkoxyaminobenzyl alcohols |
| NO126437B (en) | 1970-08-05 | 1973-02-05 | Draco Ab | |
| NL7112938A (en) | 1970-09-30 | 1972-04-05 | ||
| CH550771A (en) | 1970-10-30 | 1974-06-28 | Hoffmann La Roche | PROCESS FOR THE PRODUCTION OF PHENAETHYLAMINE DERIVATIVES. |
| US3876679A (en) | 1970-12-09 | 1975-04-08 | Aldrich Chem Co Inc | Di-substituted phenethylcarbamic acid esters |
| NL7213759A (en) | 1971-10-19 | 1973-04-25 | ||
| US4011258A (en) | 1973-06-21 | 1977-03-08 | Aktiebolaget Draco | Orally active bronchospasmolytic compounds |
| FI56673C (en) | 1974-03-29 | 1981-02-04 | Huhtamaeki Yhthymae Oy | NYTT FOERFARANDE FOER FRAMSTAELLNING AV ALFA-TERT-BYTYLAMINOMETHYL-4-HYDROXY-M-XYLEN-ALFA1 ALFA3-DIOL |
| JPS556625B2 (en) * | 1974-05-16 | 1980-02-18 | ||
| US4063025A (en) * | 1975-02-05 | 1977-12-13 | Yamanouchi Pharmaceutical Co., Ltd. | 4-Substituted amino-α-aminomethylbenzyl alcohol derivatives |
| SE7510988L (en) | 1975-10-01 | 1977-04-02 | Draco Ab | NEW PHARMACEUTICAL ACTIVE ASSOCIATIONS |
| DE2710997C3 (en) * | 1977-03-14 | 1980-08-14 | Dr. Karl Thomae Gmbh, 7950 Biberach | 4-Alkoxy carbonylamino-phenylethanolamines, their production and their use as pharmaceuticals |
-
1981
- 1981-06-30 EP EP81850117A patent/EP0043807B1/en not_active Expired
- 1981-06-30 AT AT81850117T patent/ATE7689T1/en active
- 1981-06-30 DE DE8181850117T patent/DE3163871D1/en not_active Expired
- 1981-06-30 CY CY1273A patent/CY1273A/en unknown
- 1981-07-01 US US06/279,672 patent/US4419364A/en not_active Expired - Lifetime
- 1981-07-07 NZ NZ197628A patent/NZ197628A/en unknown
- 1981-07-07 NO NO812311A patent/NO152130C/en unknown
- 1981-07-07 AU AU72618/81A patent/AU539976B2/en not_active Expired
- 1981-07-07 PH PH25872A patent/PH16535A/en unknown
- 1981-07-07 IE IE1522/81A patent/IE51373B1/en not_active IP Right Cessation
- 1981-07-08 IS IS2657A patent/IS1262B6/en unknown
- 1981-07-08 ES ES503768A patent/ES503768A0/en active Granted
- 1981-07-08 HU HU811986A patent/HU184959B/en unknown
- 1981-07-08 FI FI812158A patent/FI73666C/en not_active IP Right Cessation
- 1981-07-08 SU SU813308249A patent/SU1128830A3/en active
- 1981-07-08 PT PT73336A patent/PT73336B/en unknown
- 1981-07-08 DK DK303481A patent/DK157678C/en active
- 1981-07-08 PL PL1981232108A patent/PL128513B1/en unknown
- 1981-07-08 HU HU813788A patent/HU187611B/en unknown
- 1981-07-08 CA CA000381360A patent/CA1180021A/en not_active Expired
- 1981-07-08 CS CS815265A patent/CS221845B2/en unknown
- 1981-07-09 GR GR65453A patent/GR74291B/el unknown
- 1981-07-09 YU YU1704/81A patent/YU42116B/en unknown
- 1981-07-09 DD DD81231626A patent/DD202001A5/en unknown
- 1981-07-09 KR KR1019810002490A patent/KR850000301B1/en not_active Expired
-
1982
- 1982-06-15 ES ES513108A patent/ES513108A0/en active Granted
- 1982-06-15 ES ES513109A patent/ES8304534A1/en not_active Expired
- 1982-07-06 US US06/395,650 patent/US4451663A/en not_active Expired - Lifetime
- 1982-07-23 PH PH27617A patent/PH19447A/en unknown
-
1983
- 1983-04-15 YU YU863/83A patent/YU43168B/en unknown
- 1983-04-15 YU YU864/83A patent/YU43169B/en unknown
-
1984
- 1984-09-26 KR KR1019840005925A patent/KR850000871B1/en not_active Expired
- 1984-09-26 KR KR1019840005924A patent/KR850000870B1/en not_active Expired
- 1984-11-09 SG SG797/84A patent/SG79784G/en unknown
-
1985
- 1985-01-17 HK HK53/85A patent/HK5385A/en not_active IP Right Cessation
-
1987
- 1987-12-30 MY MY26/87A patent/MY8700026A/en unknown
-
1992
- 1992-06-24 MX MX9203239A patent/MX9203239A/en unknown
-
1993
- 1993-06-16 LU LU88304C patent/LU88304I2/en unknown
-
1996
- 1996-06-27 NO NO1996008C patent/NO1996008I1/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |